Herbicidal alkenyl sulfonamides

ABSTRACT

Alkenylsulfonylureas have been found to be effective as herbicides and plant growth regulants.

RELATED APPLICATION

This application is a division of application Ser. No. 383,323, filedJune 2, 1982, now U.S. Pat. No. 4,461,640, which is acontinuation-in-part of application U.S. Ser. No. 328,115, filed Dec. 7,1981, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to novel alkenylsulfonylureas and their use aspre- or post-emergence herbicides and plant growth regulants.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches thepreparation of compounds of Formula (i), and their use as general orselective herbicides, ##STR1## wherein R₁ and R₂ may independently bealkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2##wherein R₁ is hydrogen or lower saturated aliphatic acyl; and

R₂ is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.

The disclosed compounds are said to provide control of crabgrass, cress,endive, clover and Poa annua.

French Pat. No. 1,468,747 discloses the following para-substitutedphenylsulfonamides, useful as antidiabetic agents: ##STR3## wherein R=H,halogen, CF₃ or alkyl.

Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number ofsulfonamides, including uracil derivatives and those having the formula:##STR4## wherein R is butyl, phenyl or ##STR5## and R₁ is hydrogen ormethyl.

When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g),the compounds in which R is butyl and phenyl were most potent. Theothers were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 591633 e] describes the synthesis ofN-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide:##STR6##

U.S. Pat. No. 4,127,405 teaches compounds which are useful forcontrolling weeds in wheat having the formula: ##STR7## wherein R₁ is##STR8## R₃ and R₆ are independently hydrogen, fluorine, chlorine,bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms,nitro, trifluoromethyl, cyano, CH₃ S(O)_(n) -- or CH₃ CH₂ S(O)_(n) --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atomsor alkoxy of 1-2 carbon atom;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbonatoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Y is methyl or methoxy; or their agriculturally suitable salts; providedthat:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ isother than hydrogen and at least two of R₃, R₄, R₆ and R₇ must behydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other thanhydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine ormethyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ or R₆ mustbe hydrogen.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodneeds, such as soybeans, barley, wheat, and the like. The currentpopulation explosion and concomitant world food shortage demandimprovements in the efficiency of producing these crops. Prevention orminimizing the loss of a portion of valuable crops by killing, orinhibiting the growth of undesired vegetation is one way of improvingthis efficiency.

A wide variety of materials useful for killing, or inhibiting(controlling) the growth of undesired vegetation is available; suchmaterials are commonly referred to as herbicides. The need exists,however, for still more effective herbicides that destroy or retardweeds without causing significant damage to useful crops.

SUMMARY OF THE INVENTION

This invention relates to compounds of Formula I, suitable agriculturalsalts containing them and their method-of-use as pre-emergent orpost-emergent herbicides or plant growth modifiers. ##STR9## where L is##STR10## R is F, Cl, Br, C₁ -C₃ alkyl, CO₂ R₄, C(O)SR₈, C(O)NR₅ R₆ orS(O)_(m) R₇ ;

R₁ is H, F, Cl, Br or C₁ -C₃ alkyl;

R₂ is H, F, Cl, Br or C₁ -C₃ alkyl;

R₃ is H or CH₃ ;

R₄ is C₁ -C₄ alkyl, CH₂ CH₂ OCH₃, CH₂ CH₂ Cl or CH₂ CH═CH₂ ;

R₅ is H or C₁ -C₃ alkyl;

R₆ is C₁ -C₃ alkyl; or

R₅ and R₆ may be taken together to form --(CH₂)₄ --, --(CH₂)₅ -- or--(CH₂)₂ O(CH₂)₂ --;

R₇ is C₁ -C₃ alkyl;

R₈ is C₁ -C₄ alkyl;

m is 0, 1 or 2;

A is ##STR11## X is Cl, CH₃ or OCH₃ ; Y is CH₃, C₂ H₅, CH₂ OCH₃, OCH₃,OC₂ H₅, NH₂, NHCH₃, N(CH₃)₂, CH(OCH₃)₂ or ##STR12## Z is CH or N; X₁ isH, Cl, CH₃, OCH₃ or OC₂ H₅ ;

X₂ is CH₃, C₂ H₅, OCH₃ or OC₂ H₅ ;

X₃ is CH₃ or OCH₃ ; and

Y₁ is CH₃ or OCH₃ ;

and their agriculturally suitable salts; provided that:

(1) when R is halogen and R₁ and/or R₂ are halogen, then the values ofR, R₁ and R₂ must be the same;

(2) when R₁ and R₂ are halogen, then the values of R₁ and R₂ must be thesame;

(3) the total number of carbon atoms of R₅ and R₆ is less than or equalto 5;

(4) when X is Cl, then Z is CH and Y is OCH₃, NH₂, NHCH₃ or N(CH₃)₂ ;

(5) R₁ and R₂ are not simultaneously H; and

(6) when L is ##STR13##

Preferred for their higher herbicidal activity, greater plant growthregulant activity or more favorable ease of synthesis are:

(1) Compounds of Formula I where L is ##STR14## (2) Compounds of FormulaI where L is ##STR15## (3) Compounds of preferred 1 where: R is Cl, Br,C₁ -C₃ alkyl, CO₂ R₄ or SO₂ R₇ ;

R₄ is C₁ -C₃ alkyl; and

R₃ is H.

(4) Compounds of preferred 3 where R is CO₂ R₄.

(5) Compounds of preferred 2 where L is ##STR16## (6) Compounds ofpreferred 5 where R is CO₂ R₄ ;

R₄ is C₁ -C₃ alkyl; and

R₃ is H.

(7) Compounds of preferred 6 where A is ##STR17## (8) Compounds ofpreferred 2 where L is ##STR18## (9) Compounds of preferred 8 where R isCO₂ R₄ ;

R₄ is C₁ -C₃ alkyl; and

R₃ is H.

(10) Compounds of preferred 9 where A is ##STR19##

Specifically preferred for their highest herbicidal activity, greatestplant growth regulant activity or most favorable ease of synthesis are:

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylicacid, methyl ester;

2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylicacid, methyl ester;

2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylicacid, methyl ester;

2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylicacid, methyl ester;

2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylicacid, methyl ester; and

2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylicacid, methyl ester.

Synthesis

Many of the compounds of Formula I may be synthesized by reacting anappropriately substituted sulfonyl isocyanate of Formula II with anaminoheterocycle of Formula III as depicted in Equation 1, wherein L, R₃and A are as defined above.

Equation 1 ##STR20## The reaction is carried out in a manner analogousto that referred to by Levitt in U.S. Pat. No. 4,169,719 and U.S. Pat.No. 4,127,405.

Preparation of the appropriate sulfonyl isocyanates from thecorresponding alkenesulfonamides may be accomplished with n-butylisocyanate and phosgene in an inert solvent optionally in the presenceof 1,4-diazabicyclo[2.2.2]octane (DABCO). The reaction is depicted inEquation 2a and the procedure is again analogous to that referred to byLevitt (loc. cit.) and references therein, as well as in Levitt U.S.Pat. No. 4,238,621.

Equation 2a ##STR21##

An alternative process for preparing compounds of Formula I is to reactsulfonamides of Formula IV, optionally in the presence of a base, with aheterocyclic carbamate of Formula III'

Equation 2b ##STR22##

The reaction is carried out in an inert organic solvent such asmethylene chloride, dioxane or acetonitrile at elevated temperatures asdepicted in Equation 2b, and as disclosed in EPO publication No. 44,807.

The appropriate sulfonamides of Formula IV may be prepared by the actionof ammonia or ammonium hydroxide on a sulfonyl chloride as is widelyreported in the literature, e.g., Crossley et al., J. Am. Chem. Soc.,60, 2223 (1938). In the cases where R is a carooalkoxy group, thesulfonamides IVa may be prepared by reaction of the cyclic imide ofFormula V with the appropriate alcohol, conveniently used as thesolvent, in the presence of an acid catalyst such as sulfuric acid asdepicted in Equation 3.

Equation 3 ##STR23## Many of the 3-isothiazolone-1,1-dioxides, V, aredescribed by Lewis et al., J. Het. Chem., 8, 591 (1971).

Many of the sulfonyl chloride precursors to sulfonamides of Formula IVmay be prepared by treatment of the corresponding disulfide orbenzylthio ether with chlorine in aqueous acetic acid as described byLangler in Can. J. Chem., 54, 498 (1976). The sulfonyl chlorides inwhich R₁ and R₂ are taken together to form trimethylene ortetramethylene and R is carbomethoxy are reported by Engberts et al., J.Am. Chem. Soc., 101, 6981 (1979).

In the case of the cyclopentene derivatives where R is carbomethoxy, itis most convenient to react the sulfonyl chloride VI with ammoniumhydroxide then with aqueous sodium hydroxide to form the cyclizedcompound VII. This product is more easily purified by crystallizationthan the free sulfonamide VIII and it may be readily converted to VIIIby the methods described above.

Equation 4 ##STR24##

Other sulfonyl chloride precursors to sulfonamides of Formula IV may beprepared by reaction of the appropriate olefin with a sulfonating agent.For example, the treatment of trichloroethylene with chlorosulfonic acidproduces trichloroethenesulfonyl chloride IX as disclosed in French Pat.No. 2,094,444.

Equation 5 ##STR25##

The reaction of isobutylene with phosphorous pentachloride and sulfurtrioxide in methylene chloride affords 2-methyl-1-propene-1-sulfonylchloride as disclosed in Ger. Offen. No. 2,133,793. The synthesis of2,2-dichloroethenesulfonyl chloride is described in Zh. Obshch. Khim.,41 (11) 25-80 (1971). Also, Ger. Offen. No. 2,133,793 discloses thepreparation of 2-chloroethene-1-sulfonyl chloride. Zemlicka and Sormdescribe the preparation of 2-chloroethene-1-sulfonamide in Coll. Czech.Chem. Commun., 29, 837 (1964). 1-Bromo-1-propene-1-sulfonyl chloride isprepared as described in Ger. Offen. No. 2,000,335.

Meyers and Ho [Tetrahedron Letters, 4319 (1972)] describe thepreparation of alkenesulfonyl chlorides via a modified Ramberg-Backlundreaction as shown in Equation 6, where R' and R" are alkyl.

Equation 6 ##STR26## Compounds such as XIII and XIV may be furtherreacted to form sulfonamides of Formula IV and subsequently to ureas ofFormula I. This may be accomplished by isomerization of the double bondpresent in either IV or I to produce the desired configuration as shownin Equation 7, where R₁, R₂, R₃, R and A are as defined above.

Equation 7 ##STR27##

Photoisomerization of alkenes is widely reported in the literature; e.g.A. Schonberg, "Preparative Organic Photochemistry," [Springer-Verlag,New York, (1968)], pp. 56-57; and J. G. Calvert, J. N. Pitts,"Photochemistry," [John Wiley & Sons, New York, 1966], pp. 502-504.Often, cis and trans isomeric mixtures result from such processes andthe desired cis isomers may be isolated by crystallization, distillationor chromatography at an appropriate stage in the synthetic sequence.

Sulfides of Formula I where R is alkylthio may be prepared from thecorresponding chloro or bromo sulfonamides as shown in Equation 8, whereR₁, R₂ and R₇ are as previously defined, X' is chloro or bromo, and M isan alkali or alkaline earth metal.

Equation 8 ##STR28##

In the case of the acyclic sulfonamides of Formula IVb, an isomericmixture (XVa and XVb) may result or the undesired isomer XVb maypredominate when IVb is reacted with an alkali or alkaline earth metalsalt of an alkyl mercaptan. This would again require photoisomerizationto produce the desired isomer as discussed in Equation 7.

The preparation of compounds of Formula I where R=S(O)_(m) R₇ and m=1, 2may be accomplished as shown in Equation 9.

Equation 9 ##STR29##

The 2-alkylsulfinyl- and 2-alkylsulfonyl-1-alkene-1-sulfonylureas aremade from their corresponding 2-alkylthioalkenesulfonylureas XVI bymeans of peroxide oxidation. Reaction of the sulfidesulfonylurea XVIwith aqueous hydrogen peroxide in acetic acid at room temperature forhalf an hour affords exclusively the sulfoxidesulfonylurea XVII. If thesulfide or sulfoxide is allowed to react for 72 hours under the sameconditions, the sulfone XVIII is obtained. Oxidation for 20 hours oftenresults in a mixture of both sulfoxide and sulfone, which can be readilyseparated by column chromatography and eluted with ethylacetate/methylene chloride mixtures. Sulfonylureas described above aregenerally stable under these reaction conditions. They will however,split into heterocyclic amine and 2-alkylsulfonylalkene-1-sulfonamide ifheated. A general procedure for peroxide oxidation of sulfides tosulfones can be found in the paper by A. M. Van Arendonk and E. C.Kliderer, J. Am. Chem. Soc., 62, 3521 (1940).

The compounds of Formula I in which R is alkylthiocarbonyl [C(O)SR₈ ] orcarboxamide [C(O)NR₅ R₆ ] may be prepared from the corresponding methylester as shown in Equation 10, wherein the values of R₁, R₂, R₃, R₅, R₆,R₈ and A are as defined above.

Equation 10 ##STR30##

Alkylthiodimethylaluminum or dialkylaminodialkylaluminum is used inthese transformations as described in European Pat. No. 79-300982.0.

Sulfonamides of Formula IV in which L is2-alkoxycarbonylcyclohex-4-en-1-yl or 2-alkoxycarbonylcyclohexyl may beprepared as depicted in Equation 11, wherein R₄ is as definedpreviously.

Equation 11 ##STR31##

A mixture of excess butadiene and 3-isothiazolone-1,1-dioxide (Lewis etal., loc. cit.) is heated in the appropriate alcohol solvent, R₄ OH, inan autoclave at 100°-180°, preferably at 130° to 150° for 2 to 12 hoursto yield the sulfonamides IVc. These sulfonamides may then behydrogenated in a suitable inert solvent such as ethyl acetate with acatalyst such as palladium on carbon at ambient temperature to affordthe fully saturated sulfonamides IVd.

The synthesis of heterocyclic amines has been reviewed in "The Chemistryof Heterocyclic Compounds" a series published by Interscience Publ., NewYork and London. 2-Aminopyrimidines are described by D. J. Brown in "ThePyrimidines", Vol. XVI of this series. The 2-amino-1,3,5-triazines arereviewed by K. R. Huffman and in "The Triazines" of this same series.The synthesis of triazines are also described by F. C. Schaefer, U.S.Pat. No. 3,154,547 and by K. R. Huffman and F. C. Schaefer, J. Org.Chem., 28, 1816-1821 (1963).

Dihydrofuro[2,3-d]pyrimidine-2-amines anddihydropyrano[2,3-d]pyrimidine-2-amines andcyclopentanopyrimidine-2-amines are synthesized as described in EuropeanPat. No. 80-300505.7. The substituted 4-aminopyrimidines are disclosedin U.S. Pat. No. 4,221,585.

The preparation of 4,6-dimethylfuro[2,3-d]pyrimidine-2-amine isdescribed by E. Bisagni et al., [Bul. Soc. Chim. Fr., 803 (1969)]. Analternative procedure is depicted in Equation 12 for the case in whichR₃ is hydrogen and X₂ is methyl or ethyl.

Equation 12 ##STR32##

The keto-ester precursors XIX are prepared by well known literaturemethods, e.g., J. F. Tinker and T. E. Whatmough, J. Amer. Chem. Soc.,74, 5235 (1952).

Reacting XIX with an excess of guanidine carbonate in an organicsolvent, preferably a polar aprotic solvent such as dimethylsulfoxide(DMSO), dimethylformamide (DMF), or N,N-dimethylacetamide, at atemperature of 80° to 200°, preferably 100° to 160°, ambient pressureand preferably under an inert atmosphere, yields both XXI and XX asproducts. The products are isolated upon dilution of the reactionmixture with, for example, acetone and water successively. Higherreaction temperatures and longer reaction times (e.g., in DMSO at130°-150° for 2 to 8 hours) favor the production of the furopyrimidineXXI over the uncyclized pyrimidine XX.

The intermediates of Formula III in which X₂ is methoxy or ethoxy on2-amino-6-methylfuro[2,3-d]pyrimidine may be prepared from theappropriate malonic ester derivatives XXII, which are known in the art,as shown in Equation 13.

Equation 13 ##STR33##

In Equation 13a the diester XXII is reacted with an excess of guanidinecarbonate and heated in a suitable solvent such as ethanol or methanolat 50° to 150°, most conveniently at the boiling point of the solventchosen. The product pyrimidine XXIII is then isolated and contacted witha large excess of phosphorous oxychloride at 50° to 150°, mostconveniently at the boiling point of the reaction mixture. The dichlorocompound XXIV may be isolated by removal of the excess phosphorousoxychloride under reduced pressure, trituration of the solid residue inice-water and filtration of the product. Cyclization of XXIV occursreadily in a solvent medium comprised of water and a water-miscibleorganic solvent such as t-butanol and two equivalents of a base such asan alkali metal hydroxide with heat applied in the range of 50° to 125°.The product is conveniently isolated upon removal of the organic solventunder reduced pressure and filtration of the water-insoluble pyrimidineXXV.

The chloro compound XXV may then be converted to the alkoxy derivativeXXVI by heating with an alkali metal alkoxide, e.g., sodium methoxide inmethanol solution at temperatures of 20° to 100° C.

Heterocyclic amines of Formula IIIa in which Y is dimethoxymethyl, Z isCH and X is as defined previously are prepared as reported by W. Braker,et al., J. Am. Chem. Soc., 69, 3072 (1947), and by J. I. De Graw and V.H. Brown, J. Het. Chem., 13, 439 (1976). ##STR34##

Triazines of Formula IIIb may be prepared according to the methodsoutlined in Equations 14 and 15.

Equation 14 ##STR35## wherein Y=CH(OCH₃)₂ ; and

X=CH₃ or OCH₃.

Equation 15 ##STR36## wherein Y=CH(OCH₃)₂ ; and

X=CH₃ or OCH₃.

The reaction of Equation 14a is carried out according to the teachingsof J. M. McElvain and R. L. Clarke, J. Amer. Chem. Soc., 69, 2657(1947), in which the preparation of ethyl diethoxyiminoacetate isdescribed. The intermediate N-cyanoimidates of Formula XXIX may beprepared according to the teaching of D. Lwowski in Synthesis, 1971,263, by reacting XXVIII with cyanamide at pH 5.5, and these may becondensed according to reaction 14c with either acetamidine or O-methylisourea in an alcoholic solvent at 25° to 80° C. to provide theappropriate triazines. Alternatively, the reaction of Equation 15a,described for substituted acetonitriles by F. C. Schaefer and G. A.Peters in J. Org. Chem., 26, 412 (1961), may be used to convert nitrilesof Formula XXVII to the corresponding iminoesters. The free base may becarried on through reactions 14b and 14c, or, alternatively, convertedto the amidinium hydrochloride salts XXX as described in theaforementioned reference, and condensed with either methylN-cyanoacetimidate or with dimethyl N-cyano imidocarbonate in thepresence of one equivalent of sodium methoxide to provide the triazinesof Formula IIIb.

Cyclic acetals of Formula IIIc may be prepared from compounds of FormulaIIIa according to Equation 16 by acetal exchange.

Equation 16 ##STR37## wherein X is CH₃ or OCH₃ ; and

Z is as previously defined.

The reaction of Equation 16 is carried out by heating the acyclic acetalin an inert solvent in the presence of one equivalent of ethylene glycoland slightly more than one equivalent of a strong acid, such asp-toluenesulfonic acid with removal of the methanol formed in thereaction by distillation. The product is isolated by treatment withaqueous base, and extraction with an organic solvent, and purified bycrystallization or column chromatography.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by contacting compounds of Formula Iwith a solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g., hydroxide, alkoxide, carbonate orhydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation to another. Cationic exchange can be effected by direct treatmentof an aqueous solution of a salt of a compound of Formula I (e.g.,alkali metal or quaternary amine salt) with a solution containing thecation to be exchanged. This method is most effective when the desiredsalt containing the exchanged cation is insoluble in water, e.g., acopper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged. In this method, the cation of the resin isexchanged for that of the original salt and the desired product iseluted from the column. This method is particularly useful when thedesired salt is water soluble, e.g., a potassium, sodium or calciumsalt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The compounds of this invention and their preparation are furtherillustrated by the following examples wherein temperatures are given indegrees centigrade.

EXAMPLE 1

5,6-Dihydro-2H-cyclopenta[d]isothiazol-3(4H)-one, 1,1-Dioxide (VII)

A solution of 18 g of methyl2-(chlorosulfonyl)-1-cyclopentene-1-carboxylate in 400 ml oftetrahydrofuran was cooled to -10°, contacted with 16.2 ml ofconcentrated ammonium hydroxide, then stirred at 0° for 2.5 hours. Themixture was subsequently acidified with hydrochloric acid, extractedwith methylene chloride, then the organic phase was extracted with three100 ml portions of 1N NaOH. The combined aqueous extracts weredecolorized with activated carbon and acidified with 6N HCl, thenextracted four times with chloroform. Evaporation of the dried (Na₂ SO₄)chloroform extract left a residue which was crystallized frombenzene/chloroform to yield 4.2 g of the title compound as colorlesscrystals; m.p. 177°-179°. An infrared spectrum (nujol) exhibitedabsorptions at 3050, 1730, 1700, 1635, 1330, and 1180 cm⁻¹ ; and the NMR(90 MHz) spectrum in CDCl₃ /DMSO-d₆ solution exhibited absorptions at2.4-2.9 (m) and 11.3 (br, NH) ppm indicating the title compound.

EXAMPLE 2

Methyl 2-(Aminosulfonyl)-1-cyclopentene-1-carboxylate (VIII)

A solution of 4.2 g of 5,6-dihydro-2H-cyclopenta[d]isothiazol-3(4H)-one,1,1-dioxide in 75 ml methanol plus 0.5 ml concentrated sulfuric acid washeated to reflux for 1 hour then stirred at ambient temperature for 12hours. Sodium bicarbonate (2.1 g) was then added, the mixture wasfiltered and the filtrate evaporated in vacuo to a gelatinous mass. Thisresidue was extracted in chloroform and washed with water andsubsequently dried (Na₂ SO₄), evaporated, and crystallized fromether/hexane to afford 4.4 g of VIII as a white solid; m.p. 83°-84°. Aninfrared spectrum (nujol) exhibited absorptions at 3300, 3200, 1705,1630, 1330, 1160 cm⁻¹ and an NMR (60 MHz) spectrum in CDCl₃ solutionexhibited absorptions at 2.05 (CH₂), 2.95 (CH₂ ×2), 3.85 (CH₃ O), and5.78 (NH₂, br) ppm indicating the title compound.

EXAMPLE 3

2-Carbomethoxy-1-cyclopentene-1-sulfonyl Isocyanate

In 75 ml of dry xylenes was placed 4.0 g of methyl2-(aminosulfonyl)-1-cyclopentene-1-carboxylate (VIII), 6.5 ml of n-butylisocyanate, and 0.05 g of DABCO. The mixture was heated to reflux (ca138°) then contacted with an excess of phosgene which was condensed intothe mixture from a dry-ice condenser until the reflux temperaturedropped to 126°. Over several hours the temperaure increased to 135° andadditional phosgene was condensed into the mixture, again, lowering thetemperature to 129°. This process was repeated until no temperatureincrease could be observed, indicating complete consumption of thesulfonamide. The mixture was then cooled and the xylenes removed underreduced pressure to yield ca 5 g of an amber oil. An infrared spectrum(neat) exhibited a strong absorption at 2230 cm⁻¹ indicating the titlecompound.

EXAMPLE 4

Methyl2-[[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopenten-1-carboxylate

The sulfonyl isocyanate product (5 g) of Example 3 was diluted to aconcentration of 1.5M with dry acetonitrile and 2.0 ml of this solutionwas added to a stirred suspension of 0.31 g4-methoxy-6-methylpyrimidine-2-amine in 4.0 ml of dry acetonitrile undera nitrogen atmosphere at room temperature. After stirring several hours,the mixture was diluted with ether to precipitate the product which wascollected by filtration and dried; m.p. 161°-163°. An infrared spectrum(nujol) exhibited absorptions at 1730 and 1700 cm⁻¹, and an NMR (90 MHz)in CDCl₃ solution exhibited absorptions at 2.1 (CH₂), 2.45 (CH₃), 3.0(CH₂ ×2), 3.75 (CH₃ O), 3.95 (CH₃ O), 6.3 (CH), 7.9 (NH), 13.8 (NH), ppmindicating the title compound.

EXAMPLE 5

Methyl2-[[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylate

The sulfonyl isocyanate product of Example 3 (5 g) was diluted to aconcentration of 1.5M with dry acetonitrile and 2.0 ml of this solutionwas added to a stirred suspension of 0.27 g4,6-dimethoxy-1,3,5-triazine-2-amine in 4.0 ml dry acetonitrile under anitrogen atmosphere. The mixture was heated briefly on the steam bathuntil a homogeneous solution resulted, then stirred at ambienttemperature for 24 hours. Dilution of the mixture with etherprecipitated the product which was collected by filtration and dried to0.54 g of white crystalline solid; m.p. 168°-169°. An infrared spectrum(nujol) exhibited absorptions at 1730 and 1700 cm⁻¹ and an NMR (60 MHz)spectrum in CDCl₃ /DMSO-d₆ solution exhibited absorptions at 2.1 (CH₂),3.0 (CH₂ ×2), 3.75 (CH₃ O), 4.0 (CH₃ O×2), 9.9 (NH), 12.3 (NH) ppmindicating the title compound.

By application of Examples 1 through 5 and/or the processes describedabove, the compounds of Tables I through VII may be prepared.

                                      TABLE I                                     __________________________________________________________________________     ##STR38##                                                                    R           n  R.sub.3                                                                           X    Y         Z   m.p. (°C.)                       __________________________________________________________________________    F           4  H   CH.sub.3                                                                           CH.sub.3  CH                                          Cl          4  H   CH.sub.3                                                                           OCH.sub.3 N                                           Cl          4  H   OCH.sub.3                                                                          OCH.sub.3 CH                                          Cl          3  H   CH.sub.3                                                                           OCH.sub.3 CH                                          Cl          3  H   OCH.sub.3                                                                          OCH.sub.3 CH                                          Cl          4  H   OCH.sub.3                                                                          OCH.sub.3 N                                           Br          3  H   CH.sub.3                                                                           CH.sub.3  CH                                          Br          4  H   CH.sub.3                                                                           OCH.sub.3 CH                                          CH.sub.3    3  H   CH.sub.3                                                                           OCH.sub.3 N                                           (CH.sub.2).sub.3 H                                                                        4  H   CH.sub.3                                                                           OCH.sub.3 CH                                          C.sub.2 H.sub.5                                                                           4  H   OCH.sub.3                                                                          OCH.sub.3 CH                                          CH.sub.3    4  CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3 CH                                          CO.sub.2 CH.sub.3                                                                         3  H   CH.sub.3                                                                           CH.sub.3  CH  189-191°                         CO.sub.2 CH.sub.3                                                                         3  H   CH.sub.3                                                                           OCH.sub.3 CH  161-163°                         CO.sub.2 CH.sub.3                                                                         3  H   OCH.sub.3                                                                          OCH.sub.3 CH  177-179°                         CO.sub.2 CH.sub.3                                                                         3  H   OCH.sub.3                                                                          OCH.sub.3 N   168-169°                         CO.sub.2 CH.sub.3                                                                         3  H   CH.sub.3                                                                           OCH.sub.3 N   158-160°                         CO.sub.2 CH.sub.3                                                                         3  H   CH.sub.3                                                                           CH.sub.3  N   121-133°                         CO.sub.2 CH.sub.3                                                                         4  H   CH.sub.3                                                                           CH.sub.3  CH                                          CO.sub.2 CH.sub.3                                                                         4  H   CH.sub.3                                                                           OCH.sub.3 CH                                          CO.sub.2 CH.sub.3                                                                         4  H   OCH.sub.3                                                                          OCH.sub.3 CH                                          CO.sub.2 CH.sub.3                                                                         4  H   CH.sub.3                                                                           CH.sub.3  N                                           CO.sub.2 CH.sub.3                                                                         4  H   CH.sub.3                                                                           OCH.sub.3 N                                           CO.sub.2 CH.sub.3                                                                         4  H   OCH.sub.3                                                                          OCH.sub.3 N                                           CO.sub.2 CH.sub.3                                                                         3  H   Cl   OCH.sub.3 CH                                          CO.sub.2 CH.sub.3                                                                         4  H   Cl   NH.sub.2  CH                                          CO.sub.2 CH.sub.3                                                                         3  H   Cl   NHCH.sub.3                                                                              CH                                          CO.sub.2 CH.sub.3                                                                         4  H   Cl   N(CH.sub.3).sub.2                                                                       CH                                          CO.sub.2 CH.sub.3                                                                         3  CH.sub.3                                                                          CH.sub.3                                                                           C.sub. 2 H.sub.5                                                                        CH                                          CO.sub.2 CH.sub.3                                                                         4  H   OCH.sub.3                                                                          C.sub.2 H.sub.5                                                                         N                                           CO.sub.2 CH.sub.3                                                                         3  H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                      CH                                          CO.sub.2 CH.sub.3                                                                         4  H   OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                       CH                                          CO.sub.2 CH.sub.3                                                                         3  H   CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                        N                                           CO.sub.2 C.sub.2 H.sub.5                                                                  3  H   CH.sub.3                                                                           CH.sub.3  CH                                          CO.sub.2 C.sub.2 H.sub.5                                                                  4  H   CH.sub.3                                                                           OCH.sub.3 CH                                          CO.sub.2 CH(CH.sub.3).sub.2                                                               4  H   OCH.sub.3                                                                          OCH.sub.3 N                                           CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                        3  H   OCH.sub.3                                                                          CH.sub.3  N                                           CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                      3  H   CH.sub.3                                                                           OCH.sub.3 CH                                          CH.sub.2 CH.sub.2 Cl                                                                      4  H   OCH.sub.3                                                                          CH.sub.3  N                                           CH.sub.2 CHCH.sub.2                                                                       4  H   CH.sub.3                                                                           OCH.sub.3 CH                                          CH.sub.2 CHCH.sub.2                                                                       3  H   CH.sub.3                                                                           CH.sub.3  CH                                          C(O)SCH.sub.3                                                                             3  H   OCH.sub.3                                                                          CH.sub.3  CH                                          C(O)SCH.sub.3                                                                             4  H   CH.sub.3                                                                           CH.sub.3  CH                                          C(O)SC.sub.2 H.sub.5                                                                      3  H   OCH.sub.3                                                                          OCH.sub.3 N                                           C(O)S(CH.sub.2).sub.4 H                                                                   3  H   CH.sub.3                                                                           OCH.sub. 3                                                                              CH                                          C(O)N(CH.sub.3).sub.2                                                                     4  H   CH.sub.3                                                                           CH.sub.3  N                                           C(O)NHCH.sub.3                                                                            4  H   CH.sub.3                                                                           OCH.sub.3 N                                           C(O)N(CH.sub.3)(CH.sub.2).sub.3 H                                                         3  H   CH.sub.3                                                                           OCH.sub.3 CH                                          C(O)N(C.sub.2 H.sub.5).sub.2                                                              3  H   OCH.sub.3                                                                          OCH.sub.3 CH                                          C(O)N(CH.sub.3).sub.2                                                                     4  H   OCH.sub.3                                                                          OCH.sub.3 CH                                           ##STR39##  3  H   CH.sub.3                                                                           CH.sub.3  CH                                           ##STR40##  4  H   CH.sub.3                                                                           OCH.sub.3 CH                                           ##STR41##  3  H   OCH.sub.3                                                                          OCH.sub.3 CH                                           ##STR42##  4  CH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3  N                                           SCH.sub.3   3  H   OCH.sub.3                                                                          OCH.sub.3 CH                                          SC.sub.2 H.sub.5                                                                          4  H   OCH.sub.3                                                                          OCH.sub.3 N                                           S(CH.sub.2).sub.3 H                                                                       3  H   CH.sub.3                                                                           CH.sub.3  CH                                          S(CH.sub.2).sub.3 H                                                                       4  H   CH.sub.3                                                                           OCH.sub.3 CH                                          S(O)C.sub.2 H.sub.5                                                                       3  H   CH.sub.3                                                                           CH.sub.3  N                                           S(O)CH.sub.3                                                                              3  H   CH.sub.3                                                                           C.sub.2 H.sub.5                                                                         CH                                          SO.sub.2 CH.sub.3                                                                         4  H   CH.sub.3                                                                           OCH.sub.3 CH                                          SO.sub.2 CH.sub.3                                                                         3  H   OCH.sub.3                                                                          OCH.sub.3 CH                                          SO.sub.2 CH.sub.3                                                                         4  H   CH.sub.3                                                                           OCH.sub.3 N                                           SO.sub.2 CH.sub.3                                                                         3  H   CH.sub.3                                                                           CH.sub.3  CH                                          SO.sub.2 C.sub.2 H.sub.5                                                                  3  H   OCH.sub.3                                                                          CH.sub.3  CH                                          SO.sub.2 C.sub.2 H.sub.5                                                                  4  H   CH.sub.3                                                                           OCH.sub.3 N                                           SO.sub.2 (CH.sub.2).sub.3 H                                                               3  H   OCH.sub.3                                                                          OCH.sub.3 CH                                          SO.sub.2 (CH.sub.2).sub.3 H                                                               4  H   OCH.sub.3                                                                          OCH.sub.3 N                                           CO.sub.2 CH.sub.3                                                                         3  H   CH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                     CH                                          CO.sub.2 CH.sub.3                                                                         3  H   OCH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                                                                N                                           CO.sub.2 CH.sub.3                                                                         3  H   CH.sub.3                                                                           CH(OCH.sub.2 CH.sub.2 O)                                                                CH                                          CO.sub.2 CH.sub.3                                                                         4  H   CH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                     N                                           __________________________________________________________________________

                                      TABLE II                                    __________________________________________________________________________     ##STR43##                                                                    R       R.sub.1                                                                            R.sub.2                                                                            R.sub.3                                                                          X   Y    Z  m.p. (°C.)                            __________________________________________________________________________    F       F    F    H  OCH.sub.3                                                                         OCH.sub.3                                                                          CH                                              Cl      Cl   Cl   H  OCH.sub.3                                                                         CH.sub.3                                                                           CH 165-167°                              Br      Br   Br   H  CH.sub.3                                                                          CH.sub.3                                                                           CH                                              Br      Br   H    H  CH.sub.3                                                                          OCH.sub.3                                                                          N                                               Cl      Cl   H    H  OCH.sub.3                                                                         OCH.sub.3                                                                          N                                               CH.sub.3                                                                              CH.sub.3                                                                           H    H  OCH.sub.3                                                                         OCH.sub.3                                                                          CH                                              C.sub.2 H.sub.5                                                                       Cl   H    H  CH.sub.3                                                                          OCH.sub.3                                                                          CH                                              (CH.sub.2).sub.3 H                                                                    H    CH.sub.3                                                                           H  CH.sub.3                                                                          OCH.sub.3                                                                          N                                               CH.sub.3                                                                              CH.sub.3                                                                           H    H  OCH.sub.3                                                                         OCH.sub.3                                                                          N                                               C.sub.2 H.sub.5                                                                       H    (CH.sub.2).sub.3 H                                                                 H  CH.sub.3                                                                          OCH.sub.3                                                                          CH                                              CH(CH.sub.3).sub.2                                                                    H    C.sub.2 H.sub.5                                                                    H  CH.sub.3                                                                          OCH.sub.3                                                                          N                                               CH.sub.3                                                                              CH.sub.3                                                                           H    H  CH.sub.3                                                                          CH.sub.3                                                                           CH                                              Cl      CH.sub.3                                                                           H    H  CH.sub.3                                                                          CH.sub.3                                                                           N                                               CH.sub.3                                                                              Cl   H    CH.sub.3                                                                         CH.sub.3                                                                          OCH.sub.3                                                                          CH                                              CH.sub.3                                                                              (CH.sub.2).sub.3 H                                                                 H    H  CH.sub.3                                                                          CH.sub.3                                                                           CH                                              CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                           H    H  CH.sub.3                                                                          CH.sub.3                                                                           CH                                              CO.sub.2 CH.sub.3                                                                     H    CH.sub.3                                                                           H  CH.sub.3                                                                          OCH.sub.3                                                                          CH                                              CO.sub.2 CH.sub.3                                                                     C.sub.2 H.sub.5                                                                    H    H  OCH.sub.3                                                                         OCH.sub.3                                                                          CH                                              CO.sub.2 CH.sub.3                                                                     H    C.sub.2 H.sub.5                                                                    H  OCH.sub.3                                                                         OCH.sub.3                                                                          N                                               CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                           H    H  OCH.sub.3                                                                         CH.sub.3                                                                           N                                               CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                           CH.sub.3                                                                           H  OCH.sub.3                                                                         CH.sub.3                                                                           N                                               CO.sub.2 CH.sub.3                                                                     Br   H    H  OCH.sub.3                                                                         OCH.sub.3                                                                          CH                                              CO.sub.2 CH.sub.3                                                                     Cl   Cl   H  OCH.sub.3                                                                         OCH.sub.3                                                                          N                                               CO.sub.2 C.sub.2 H.sub.5                                                              H    CH.sub.3                                                                           H  CH.sub.3                                                                          CH.sub.3                                                                           CH                                              CO.sub.2 (CH.sub.2).sub.4 H                                                           H    Cl   H  CH.sub.3                                                                          CH.sub.3                                                                           N                                               C(O)SCH.sub.3                                                                         H    CH.sub.3                                                                           H  CH.sub.3                                                                          OCH.sub.3                                                                          CH                                              Cl      Cl   Cl   H  CH.sub.3                                                                          CH.sub.3                                                                           CH 157-160°                              Cl      Cl   Cl   H  OCH.sub.3                                                                         OCH.sub.3                                                                          CH 178-179°                              Cl      Cl   Cl   H  OCH.sub.3                                                                         CH.sub.3                                                                           N  140-141°                              Cl      Cl   Cl   H  OCH.sub.3                                                                         OCH.sub.3                                                                          N  153-155°                              C(O)N(CH.sub.3).sub.2                                                                 H    CH.sub.3                                                                           H  CH.sub.3                                                                          OCH.sub.3                                                                          N                                                ##STR44##                                                                            H    CH.sub.3                                                                           H  OCH.sub.3                                                                         OCH.sub.3                                                                          CH                                              C(O)N(C.sub.2 H.sub.5).sub.2                                                          C.sub.2 H.sub.5                                                                    H    H  OCH.sub.3                                                                         CH.sub.3                                                                           CH                                              SCH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H  Cl  OCH.sub.3                                                                          CH                                              SC.sub.2 H.sub.5                                                                      H    C.sub.2 H.sub.5                                                                    H  CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                  CH                                              S(O)(CH.sub.2).sub.3 H                                                                H    CH.sub.3                                                                           H  CH.sub.3                                                                          OCH.sub.3                                                                          N                                               S(O)CH.sub.3                                                                          H    CH.sub.3                                                                           H  OCH.sub.3                                                                         OCH.sub.3                                                                          CH                                              SO.sub.2 CH.sub.3                                                                     H    Cl   H  CH.sub.3                                                                          CH.sub.3                                                                           CH                                              SO.sub.2 (CH.sub.2).sub.3 H                                                           H    Cl   H  CH.sub.3                                                                          OCH.sub.3                                                                          N                                               SO.sub.2 CH.sub.3                                                                     Cl   Cl   H  OCH.sub.3                                                                         OCH.sub.3                                                                          N                                               __________________________________________________________________________

                  TABLE III                                                       ______________________________________                                         ##STR45##                                                                    R         R.sub.3                                                                              n      p   X.sub.1                                                                              Q    m.p. (°C.)                     ______________________________________                                        Cl        H      3      2   CH.sub.3                                                                             O                                          Cl        H      4      3   OCH.sub.3                                                                            O                                          Cl        H      3      3   CH.sub.3                                                                             O                                          F         H      4      2   CH.sub.3                                                                             CH.sub.2                                   Br        H      4      3   OCH.sub.3                                                                            O                                          CH.sub.3  H      3      3   CH.sub.3                                                                             O                                          C.sub.2 H.sub.5                                                                         H      3      2   OC.sub.2 H.sub.5                                                                     O                                          CH.sub.3  CH.sub.3                                                                             4      2   CH.sub.3                                                                             CH.sub.2                                   CO.sub.2 CH.sub.3                                                                       H      4      3   CH.sub.3                                                                             O                                          CO.sub.2 CH.sub.3                                                                       H      3      2   OCH.sub.3                                                                            O                                          CO.sub.2 CH.sub.3                                                                       H      3      3   CH.sub.3                                                                             O                                          CO.sub.2 CH.sub.3                                                                       H      4      2   CH.sub.3                                                                             CH.sub.2                                   CO.sub.2 CH.sub.3                                                                       H      4      3   Cl     O                                          CO.sub.2 CH.sub.3                                                                       H      3      2   H      O                                          CO.sub.2 C.sub.2 H.sub.5                                                                H      3      3   CH.sub.3                                                                             O                                          C(O)N(CH.sub.3).sub.2                                                                   H      3      2   CH.sub.3                                                                             O                                           ##STR46##                                                                              H      4      2   CH.sub.3                                                                             CH.sub.2                                   SCH.sub.3 H      4      3   CH.sub.3                                                                             O                                          SO.sub.2 CH.sub.3                                                                       H      3      3   OCH.sub.3                                                                            O                                          S(O)C.sub.2 H.sub.5                                                                     H      3      2   CH.sub.3                                                                             O                                          SO.sub.2 C.sub.2 H.sub.5                                                                H      4      2   OCH.sub.3                                                                            CH.sub.2                                   C(O)SCH.sub.3                                                                           H      3      2   CH.sub.3                                                                             O                                          ______________________________________                                    

                  TABLE IV                                                        ______________________________________                                         ##STR47##                                                                    R          n        R.sub.3 X.sub.2 m.p. (°C.)                         ______________________________________                                        Cl         2        H       CH.sub.3                                          Cl         2        H       C.sub.2 H.sub.5                                   Cl         3        H       CH.sub.3                                          Br         3        H       OCH.sub.3                                         F          2        H       OC.sub.2 H.sub.5                                  CH.sub.3   2        H       CH.sub.3                                          C.sub.2 H.sub.5                                                                          3        H       OCH.sub.3                                         CH.sub.3   3        H       CH.sub.3                                          CO.sub.2 CH.sub.3                                                                        2        H       CH.sub.3                                          CO.sub.2 CH.sub.3                                                                        2        H       OCH.sub.3                                         CO.sub.2 CH.sub.3                                                                        3        H       CH.sub.3                                          CO.sub.2 CH.sub.3                                                                        3        H       OCH.sub.3                                         CO.sub.2 CH.sub.3                                                                        2        CH.sub.3                                                                              CH.sub.3                                          CO.sub.2 CH.sub.3                                                                        3        H       CH.sub.3                                          CO.sub.2 C.sub.2 H.sub.5                                                                 2        H       CH.sub.3                                          C(O)N(CH.sub.3).sub.2                                                                    2        H       OCH.sub. 3                                         ##STR48## 3        H       CH.sub.3                                          C(O)SCH.sub.3                                                                            3        H       CH.sub.3                                          SCH.sub.3  2        H       OCH.sub.3                                         SO.sub.2 CH.sub.3                                                                        2        H       CH.sub.3                                          S(O)CH.sub.3                                                                             3        H       OCH.sub.3                                         SO.sub.2 C.sub.2 H.sub.5                                                                 3        H       CH.sub.3                                          ______________________________________                                    

                  TABLE V                                                         ______________________________________                                         ##STR49##                                                                    R        n       R.sub.3 X.sub.3                                                                              Y.sub.1                                                                              m.p. (°C.)                      ______________________________________                                        Cl       3       H       CH.sub.3                                                                             CH.sub.3                                      Cl       2       H       OCH.sub.3                                                                            CH.sub.3                                      Cl       3       H       CH.sub.3                                                                             OCH.sub.3                                     Br       2       H       CH.sub.3                                                                             CH.sub.3                                      F        3       H       CH.sub.3                                                                             OCH.sub.3                                     CH.sub.3 2       H       OCH.sub.3                                                                            CH.sub.3                                      C.sub.2 H.sub.5                                                                        3       H       CH.sub.3                                                                             CH.sub.3                                      CH.sub.3 3       H       OCH.sub.3                                                                            CH.sub.3                                      CO.sub.2 CH.sub.3                                                                      3       H       OCH.sub.3                                                                            OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                      3       H       CH.sub.3                                                                             OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                      2       H       OCH.sub.3                                                                            CH.sub.3                                      CO.sub.2 CH.sub.3                                                                      2       H       CH.sub.3                                                                             CH.sub.3                                      CO.sub.2 CH.sub.3                                                                      3       CH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3                                      CO.sub.2 CH.sub.3                                                                      2       H       OCH.sub.3                                                                            CH.sub.3                                      CO.sub.2 C.sub.2 H.sub. 5                                                              3       H       CH.sub.3                                                                             OCH.sub.3                                     C(O)N(CH.sub.3).sub.2                                                                  2       H       CH.sub.3                                                                             CH.sub.3                                       ##STR50##                                                                             2       H       CH.sub.3                                                                             OCH.sub.3                                     C(O)SCH.sub.3                                                                          3       H       OCH.sub.3                                                                            CH.sub.3                                      SCH.sub.3                                                                              3       H       CH.sub.3                                                                             CH.sub.3                                      SO.sub.2 CH.sub.3                                                                      2       H       CH.sub.3                                                                             CH.sub.3                                      S(O)CH.sub.3                                                                           2       H       OCH.sub.3                                                                            CH.sub.3                                      SO.sub.2 C.sub.2 H.sub.5                                                               3       H       OCH.sub.3                                                                            CH.sub.3                                      ______________________________________                                    

                  TABLE VI                                                        ______________________________________                                         ##STR51##                                                                    R.sub.4   R.sub.3                                                                              X       Y        Z    m.p. (°C.)                      ______________________________________                                        CH.sub.3  H      CH.sub.3                                                                              CH.sub.3 CH   170-171°                        CH.sub.3  H      CH.sub.3                                                                              OCH.sub.3                                                                              CH   185-186°                        CH.sub.3  H      OCH.sub.3                                                                             OCH.sub.3                                                                              CH   177-178°                        CH.sub.3  H      CH.sub.3                                                                              OCH.sub.3                                                                              N    147-149°                        CH.sub.3  H      OCH.sub.3                                                                             OCH.sub.3                                                                              N    152-154°                        CH.sub.3  H      Cl      OCH.sub.3                                                                              CH                                          CH.sub.3  CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                              CH                                          C.sub.2 H.sub.5                                                                         H      OCH.sub.3                                                                             OCH.sub.3                                                                              N                                           CH(CH.sub.3).sub.2                                                                      H      CH.sub.3                                                                              OCH.sub.3                                                                              N                                           CH(CH.sub.3)C.sub.2 H.sub.5                                                             H      CH.sub.3                                                                              OCH.sub.3                                                                              CH                                          CH.sub.2 CH.sub.2 Cl                                                                    H      OCH.sub.3                                                                             OCH.sub.3                                                                              CH                                          CH.sub.2 CH.sub.2 OCH.sub. 3                                                            H      OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                                                     CH                                          CH.sub.2 CHCH.sub.2                                                                     H      CH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                    CH                                          ______________________________________                                    

                  TABLE VII                                                       ______________________________________                                         ##STR52##                                                                    R.sub.4   R.sub.3                                                                              X       Y        Z    m.p. (°C.)                      ______________________________________                                        CH.sub.3  H      CH.sub.3                                                                              CH.sub.3 CH                                          CH.sub.3  H      CH.sub.3                                                                              OCH.sub.3                                                                              CH   151-153°                        CH.sub.3  H      OCH.sub.3                                                                             OCH.sub.3                                                                              CH   152-154°                        CH.sub.3  H      OCH.sub.3                                                                             CH.sub.3 N    168-170°                        CH.sub.3  H      OCH.sub.3                                                                             OCH.sub.3                                                                              N    172-175°                        CH.sub.3  H      Cl      OCH.sub.3                                                                              CH                                          CH.sub.3  CH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                              CH                                          CH.sub.3  H      OCH.sub.3                                                                             NHCH.sub.3                                                                             CH                                          C.sub.2 H.sub.5                                                                         H      CH.sub.3                                                                              OCH.sub.3                                                                              N                                           CH(CH.sub.3).sub.2                                                                      H      CH.sub.3                                                                              OCH.sub.3                                                                              CH                                          CH(CH.sub.3)C.sub.2 H.sub.5                                                             H      OCH.sub.3                                                                             OCH.sub.3                                                                              N                                           CH.sub.2 CH.sub.2 Cl                                                                    H      OCH.sub.3                                                                             CH.sub.3 CH                                          CH.sub.2 CH.sub.2 OCH.sub.3                                                             H      CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                                                     CH                                          CH.sub.2 CHCH.sub.2                                                                     H      CH.sub.3                                                                              CH(OCH.sub.3).sub.2                                                                    CH                                          ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

                  TABLE VIII                                                      ______________________________________                                                     Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                             Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                             20-90      0-74    1-10                                        Oil Suspensions,                                                                              3-50     40-95    0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                           10-50     40-84    1-20                                        Dusts           1-25     70-99    0-5                                         Granules and Pellets                                                                         0.1-95      5-99.9 0-15                                        High Strength  90-99      0-10    0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 6

Wettable Powder

    ______________________________________                                        2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]amino-                                                     80%                                                sulfonyl]-1-cyclopentene-1-carboxylic acid,                                   methyl ester                                                                  sodium alkylnaphthalenesulfonate                                                                         2%                                                 sodium ligninsulfonate     2%                                                 synthetic amorphous silica 3%                                                 kaolinite                  13%                                                ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 7

Wettable Powder

    ______________________________________                                        2-[[ (4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                   50%                                                aminosulfonyl]-1-cyclopentene-1-carboxylic acid,                              methyl ester                                                                  sodium alkylnaphthalenesulfonate                                                                         2%                                                 low viscosity methyl cellulose                                                                           2%                                                 diatomaceous earth         46%                                                ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 8

Granule

    ______________________________________                                        Wettable Powder of Example 7                                                                          5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 9

Extruded Pellet

    ______________________________________                                        2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-                                                     25%                                                aminosulfonyl]-1-cyclopentene-1-carboxylic acid,                              methyl ester                                                                  anhydrous sodium sulfate   10%                                                crude calcium ligninsulfonate                                                                             5%                                                sodium alkylnaphthalenesulfonate                                                                          1%                                                calcium/magnesium bentonite                                                                              59%                                                ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 10

Oil Suspension

    ______________________________________                                        2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                                    25%                                                sulfonyl]-1-cyclopentene-1-carboxylic acid,                                   methyl ester                                                                  polyoxyethylene sorbitol hexaoleate                                                                       5%                                                highly aliphatic hydrocarbon oil                                                                         70%                                                ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 11

Wettable Powder

    ______________________________________                                        2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-                                                     20%                                                bonyl]aminosulfonyl]-1-cyclopentene-1-carboxylic                              acid, methyl ester                                                            sodium alkylnaphthalenesulfonate                                                                         4%                                                 sodium ligninsulfonate     4%                                                 low viscosity methyl cellulose                                                                           3%                                                 attapulgite                69%                                                ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 12

Low Strength Granule

    ______________________________________                                        2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-                                                     1%                                                 aminosulfonyl]-1-cyclopentene-1-carboxylic acid;                              methyl ester                                                                  N,N--dimethylformamide     9%                                                 attapulgite granules       90%                                                (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 13

Aqueous Suspension

    ______________________________________                                        2[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                     40%                                                aminosulfonyl]-1-cyclopentene-1-carboxylic acid,                              methyl ester                                                                  polyacrylic acid thickener 0.3%                                               dodecylphenol polyethylene glycol ether                                                                  0.5%                                               disodium phosphate          1%                                                monosodium phosphate       0.5%                                               polyvinyl alcohol          1.0%                                               water                      56.7%                                              ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 14

Solution

    ______________________________________                                        2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-                                                           5%                                                amino-sulfonyl]-1-cyclopentene-1-carboxylic acid,                             methyl ester, sodium salt                                                     water                      95%                                                ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 15

Low Strength Granule

    ______________________________________                                        2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-                                                      0.1%                                              aminosulfonyl]-1-cyclopentene-1-carboxylic acid,                              methyl ester                                                                  attapulgite granules       99.9%                                              (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 16

Granule

    ______________________________________                                        2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                    80%                                                aminosulfonyl]-1-cyclopentene-1-carboxylic acid,                              methyl ester                                                                  wetting agent               1%                                                crude ligninsulfonate salt (containing                                                                   10%                                                5-20% of the natural sugars)                                                  attapulgite clay            9%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 17

High Strength Concentrate

    ______________________________________                                        2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                                     99%                                               sulfonyl]-1-cyclopentene-1-carboxylic acid,                                   methyl ester                                                                  silica aerogel             0.5%                                               synthetic amorphous silica 0.5%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 18

Wettable Powder

    ______________________________________                                        2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocar-                                                           90%                                               bonyl]aminosulfonyl]-1-cyclopentene-carboxylic                                acid, methyl ester                                                            dioctyl sodium sulfosuccinate                                                                            0.1%                                               synthetic fine silica      9.9%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 19

Wettable Powder

    ______________________________________                                        2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-                                                     40%                                                bonyl]aminosulfonyl]-1-cyclopentene-1-carboxylic                              acid, methyl ester                                                            sodium ligninsulfonate     20%                                                montmorillonite clay       40%                                                ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 20

Oil Suspension

    ______________________________________                                        2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]amino-                                                     35%                                                sulfonyl]-1-cyclopentene-1-carboxylic acid,                                   methyl ester                                                                  blend of polyalcohol carboxylic                                                                           6%                                                esters and oil soluble petroleum                                              sulfonates                                                                    xylene                     59%                                                ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 21

Dust

    ______________________________________                                        2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                    10%                                                aminosulfonyl]-1-cyclopentene-1-carboxylic acid,                              methyl ester                                                                  attapulgite                10%                                                Pyrophyllite               80%                                                ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

Utility

The compounds of the present invention are powerful herbicides. Theyhave utility for broad-spectrum pre- and/or post-emergence weed controlin areas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,parking lots, drive-in theaters, around billboards, highway and railroadstructures. Alternatively, the subject compounds are useful for plantgrowth modification, such as defoliation and growth retardation.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as selective orgeneral herbicides, the crop species involved, the types of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.06 to 10kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for plant growth modificationor for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory(Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean,sugarbeet, rice, wheat and nutsedge tubers (Cyperus rotundus) wereplanted in a growth medium and treated pre-emergence with the chemicalsdissolved in a non-phytotoxic solvent. At the same time, cotton havingfive leaves (including cotyledonary ones), bush beans with the thirdtrifoliolate leaf expanding, crabgrass, barnyardgrass and wild oats withtwo leaves, cassia with three leaves (including cotyledonary ones),morningglory and cocklebur with four leaves (including the cotyledonaryones), sorghum and corn with four leaves, soybean with two cotyledonaryleaves, rice with three leaves, wheat with one leaf, sugarbeets with twoleaves, and nutsedge with three to five leaves were sprayed. Treatedplants and controls were maintained in a greenhouse for sixteen days,whereupon all species were compared to controls and visually rated forresponse to treatment. The ratings are based on a numerical scaleextending from 0=no injury, to 10=complete kill. The accompanyingdescriptive symbols have the following meanings:

C=chlorosis/necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

S=albinism; and

U=unusual pigmentation;

6Y=abscised buds or flowers.

The ratings for the compounds tested by this procedure are presented inTable A. It will be seen that certain of the compounds tested are highlyactive pre- and/or post-emergence herbicides and/or possess plant growthmodifying properties.

    ______________________________________                                        Table Structures                                                              ______________________________________                                        Compound 1                                                                              ##STR53##                                                           Compound 2                                                                              ##STR54##                                                           Compound 3                                                                              ##STR55##                                                           Compound 4                                                                              ##STR56##                                                           Compound 5                                                                              ##STR57##                                                           Compound 6                                                                              ##STR58##                                                           Compound 7                                                                              ##STR59##                                                           Compound 8                                                                              ##STR60##                                                           Compound 9                                                                              ##STR61##                                                           Compound 10                                                                             ##STR62##                                                           Compound 11                                                                             ##STR63##                                                           Compound 12                                                                             ##STR64##                                                           Compound 13                                                                             ##STR65##                                                           Compound 14                                                                             ##STR66##                                                           Compound 15                                                                             ##STR67##                                                           Compound 16                                                                             ##STR68##                                                           Compound 17                                                                             ##STR69##                                                           Compound 18                                                                             ##STR70##                                                           Compound 19                                                                             ##STR71##                                                           Compound 20                                                                             ##STR72##                                                       

    TABLE A       Compound 1 Cmpd. 2 Cmpd 3 Cmpd. 4 Compound 5 Cmpd. 6 Cmpd. 7 Compound     8  Compound 9 Cmpd. 10 Compound 11 Cmpd. 12 Rate kg/ha 0.4 .05 .05 .05     .05 0.4 .05 .05 .05 0.4 .05 .05 2 .05 .05 2 0.4       POST-EMERGENCE Bush bean 9D,9G,6Y 6D,8G,6Y 7D,8G,6Y 6D,6G,6Y 4C,9G,6Y     9C 9D,9G,6Y 3C,7G,6Y 0 2G 2G 1C  2C,3G 0 1C 4C 3C,6Y Cotton 4C,9G 1C,6G     2C,7G 1C,6G 5G 4C,9G 3C,8G 1C,5G 0 0 0 0 1C 0 1C 2C 2C Morningglory     3C,8G 2C,6G 2C,5G 2C,7G 3G 3C,8G 1C,4G 2C,5G 0 1C 2H 0 1C,3G 0 0 2C 1C     Cocklebur 9C 3C,9H 2C,9H 5C,9G 0 10C 2C,6G 1C,5H 0 5C,9G 2H 1C 4C,8G 0     4G 9C 9C Cassia 2C,5G 2C,5G 1C,4G 2C,4G 0 3C,8H 3C 1C 0 0 0 0 1C 0 1C 2C     1C Nutsedge 9C 3C,9G 3C,9G 3C,9G 2G 5C,9G 0 1C,3G 0 0 3C,5G 0 3C,9G 0 0     1C,4G 0 Crabgrass 9C 2C,8G 2C,9H 2C,9G 0 7C,9G 2G 1C 0 0 0 0 2C 0 0     1C,4G 0 Barnyardgrass 10C 9C 9C 9C 0 9C 3C,9H 3C,9H 0 0 0 0 3C,8H 0 0     3C,9H 0 Wild Oats 9C 3C,9H 2C,9H 3C,9G 0 3C,9G 0 2C 0 0 0 0 0 0 0 0 0     Wheat 5C,9G 1C,6G 3C,9H 3C,9G 0 6C,9G 1C,2G 2C,5G 0 0 0 0 0 0 0 0 0 Corn     5U,9C 1U,9G 2C,9G 2U,9G 2C,8H 6C,9G 2U,9G 5C,9G 0 0 0 1H 9H 0 3H 2C,8H     2C,2H Soybean 4C,9G 2C,5H 2C,7H 3C,7H 1C,5H 6C,9H 1C,8H 2C,9G,5X 0 0 0 0     1H 0 0 1C 1C,1H Rice 6C,9G 2C,9G 4C,9G 5C,9G 5G 5C,9G 4C,9G 4C,9G 0 0 0     0 2C,7G 0 0 2C,6G 1C Sorghum 9C 3C,9G 5C,9G 8C,9G 2C,9H 5U,9G 2C,9H     3C,9G 0 0 0 0 3C,8H 0 2G 3C,9G 1C,3G Sugarbeet -- -- -- -- -- -- -- --     -- -- -- -- -- -- -- -- -- PRE-EMERGENCE Morningglory 6G 1C,6G 1C,6G     3C,6G 0 3C,7G 1C,4G 2C,5H 0 1H 0 0  8G 0 2C,6H 8G 1C Cocklebur 9H 2C,9H     9H 2C,9H 0 9H 9C 9H 3H 6G 4G 0 8H 0 7H 9H 9H Cassia 2C,8G 1C,5G 2C,8G     3C,8G 0 3C,9G 2C,8G 2C,7G 0 8G 0 0 2G 0 6G -- 3G Nutsedge 10E 2C,9G 9G     10E 0 2C,6G 2G 6G 0 0 0 0 8G 0 0 7G 0 Crabgrass 2C,6G 1C 2C,6G 3C,7G 0     2C,5G 1C 0 0 0 0 0 2G 0 3G 5G 0 Barnyardgrass 3C,9H 3C,9H 5C,9H 5C,9H 0     5C,9H 1C 2C,6H 0 0 0 0 2C,8G 0 2G 5G 2C Wild Oats 5C,9H 2C,9G 5C,9G     3C,9G 0 3C,9G 1C,4G 0 0 0 0 0 0 0 0 0 0 Wheat 3C,9H 1C,9H 9H 2C,9G 0     1C,9G 1C,4G 0 0 0 0 0 3G 0 0 3G 0 Corn 10H 2C,9H 5C,9H 2C,9G 2C,7G 9H     3C,9H 3C,9H 0 0 0 2C 9G 0 1C,3G 2C,9G 1C,3G Soybean 6H 2C,5G 3C,7H 3C,6H     0 9H 3C,8H 2C,7H 0 0 0 0 0 0 0 1H 1C Rice 10E 2C,8H 10E 10E 2C,7G 10E     3C,9H 5C,9H 0 0 0 0 8H 0 0 2G 0 Sorghum 5C,9H 7C,9H 8C,9H 2C,9H 3C,8H     6C,9H 3C,9H 3C,9H 0 0 0 0 3C,8G 0 0 2C,9G 0 Sugarbeet -- -- -- -- -- --     -- -- -- -- -- -- -- -- -- -- 0       Compound 13 Cmpd. 14 Cmpd. 15 Cmpd. 16Cmpd. 17 Cmpd. 18 Cmpd. 19     Compound 20 Rate kg/ha 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 2       POST-EMERGENCE Bush bean 4C,6Y 4S,5G,6Y 4S,6G,6Y 4C,8G,6Y 3C,9G,6Y 1H     3C,6G,6Y 3C,5G,6Y 2C,2H 5C,3H,6Y Cotton 2C 2C 2C 1C 2C,3H 1B 2C,2H 2C,3G     2C 1C Morningglory 1C 2 2C,6H 3C,5H 2C,3H 2C 3C,7H 3C,8H 3C,5H 3C,5H     Cocklebur 2C,8G 10C 2C,5G 9C 2H 0 1C 3C,4G 0 0 Cassia 1C 2C,4G 3C,5G 2C     2C 1C 2C 2C 1C 3C Nutsedge 0 5G 0 3G 0 0 1C,4G 0 0 0 Crabgrass 0 4G 2C 0     1C 0 0 0 0 0 Barnyardgrass 0 2C,6H 2C 0 1C,2H 0 2C,5H 0 0 1C,3H Wild     Oats 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 Corn 0 0 0 2G 0 0 2G     2C 0 0 Soybean 1C,2H 2C,5H 2H 1H 1C 1C 3C,2H 2C,2H 4C,4G 3C Rice 0 1C,5G     5G 0 0 0 2C,5G 1C,3G 3G 0 Sorghum 1C,3G 2C,9H 4G 0 0 0 2C,5G 0 2G 2C     Sugarbeet -- -- -- -- -- 1C 2C,3H 4C,8G 3C,7G 3C,6G PRE-EMERGENCE     Morningglory 2G 2C,7G 1C 1C,1H 1C 2C 2C,7G 1C,4G 3C,3H 3C,6G Cocklebur     8H 9H 8H 8H 8H -- 8H 0 -- 7H Cassia 4G 5H 2C 0 0 2H 2C,5H 0 2C 1C     Nutsedge 0 0 7G 0 0 0 10E 0 0 0 Crabgrass 0 0 1C 2C 0 0 2G 0 0 0     Barnyardgrass 1C 3C,5H 2C 1C 0 0 2C 0 0 0 Wild Oats 0 2C,6G 0 0 0 0 2C 0     0 0 Wheat 0 2C,7G 0 0 0 0 0 0 0 0 Corn 1C,3G 2C,7H 1C,4G 0 0 0 2C,5G 0 0     2C Soybean 2G 1C,2H 0 0 0 0 0 0 0 1C Rice 2G 2C,8H 0 0 0 0 0 0 0 1C     Sorghum 0 2C,8G 0 0 0 0 1C 0 5G 2G Sugarbeet 0 2C,8G 3G 0 0 5G 0 0 7G

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsingtonsilt loam soil. One pan was planted with corn, sorghum, Kentuckybluegrass and several grassy weeds. The other pan was planted withcotton, soybeans, purple nutsedge (Cyperus rotundus), and severalbroadleaf weeds. The following grassy and broadleaf weeds were planted:crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur(Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory(Ipomoea hederacea), sicklepod (Cassia obtusifolia), teaweed (Sidaspinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Daturastramonium). A 12.5 cm diameter plastic pot was also filled withprepared soil and planted with rice and wheat. Another 12.5 cm pot wasplanted with sugarbeets. The above four containers were treatedpre-emergence with several test compounds within the scope of theinvention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B. Note the high herbicidal activity of the compounds tested atthe low rates of application selected for this evaluation.

                                      TABLE B                                     __________________________________________________________________________    PRE-EMERGENCE ON                                                              FALLSINGTON SILT LOAM                                                                 Compound 1                                                                            Compound 2                                                                            Compound 3                                                                            Compound 5                                                                           Compound 6                             Rate kg/ha                                                                            0.03                                                                              0.12                                                                              0.03                                                                              0.12                                                                              0.03                                                                              0.12                                                                              0.03                                                                              0.12                                                                              0.03                                                                              0.12                              __________________________________________________________________________    Crabgrass                                                                             4G  7G  6G  8G  6G  7G  0   5G  2G  3G                                Barnyardgrass                                                                         8G,5H                                                                             9G,9C                                                                             9G,9C                                                                             10C 8G,3H                                                                             10C 5G  6G  4G  6G                                Sorghum --  --  --  --  --  --  8G,3H                                                                             9G,3H                                                                             6G,3H                                                                             8G,3H                             Wild Oats                                                                             6G  7G,3H                                                                             7G,3H                                                                             7G,3H                                                                             7G,3H                                                                             7G,3H                                                                             2G  3G  0   3G                                Johnsongrass                                                                          8G,5H                                                                             8G,5H                                                                             9G,5H                                                                             9G,5H                                                                             8G,3H                                                                             8G,3H                                                                             3G,2H                                                                             5G,3H                                                                             3G,2H                                                                             5G,3H                             Dallisgrass                                                                           8G  8G,3H                                                                             9G  9G,3H                                                                             8G  8G  0   0   0   0                                 Giant foxtail                                                                         3G  5G  8G,3H                                                                             9G,9C                                                                             8G,5H                                                                             9G,9C                                                                             0   3G,3C                                                                             2G  5G,5C                             Ky. bluegrass                                                                         7G  8G,8C                                                                             10C 10C 10E 10E 2G  10C 7G,3H                                                                             7G,5H                             Cheatgrass                                                                            7G,3H                                                                             9G,9C                                                                             10C 10C 10C 10C 3H  5G,3H                                                                             0   4G                                Sugarbeets                                                                            7G,5H                                                                             9G,8C                                                                             8G,8C                                                                             9G,9C                                                                             7G,5H                                                                             8G,8C                                                                             8G,8C                                                                             9G,9C                                                                             8G,7C                                                                             9G,9C                             Corn    5G,2H                                                                             8G,5H                                                                             7G,5H                                                                             8G,5H                                                                             8G,5H                                                                             10C 5G,2H                                                                             8G,5H                                                                             4G  7G,5H                             Mustard 8G  9G,5C                                                                             9G,8C                                                                             10C 9G,7C                                                                             10C 8G,3C                                                                             9G,9C                                                                             8G,3H                                                                             9G,8C                             Cocklebur                                                                             4G  5G  6G  --  5G  7G,2C                                                                             4G  6G  4G  6G                                Pigweed 7G  8G,8E                                                                             10E 10E 10E 10E 10C 10C 9G,8C                                                                             10E                               Nutsedge                                                                              6G  10E 8G  10E 10E 10E 0   4G  4G  5G                                Cotton  5G  8G,5H                                                                             8G,5H                                                                             9G,5H                                                                             6G  8G,3H                                                                             7G,3H                                                                             8G,5H                                                                             7G  7G,3H                             Morningglory                                                                          3G,2C                                                                             5G,2C                                                                             4G,3H                                                                             5G,3H                                                                             4G  4G  3G  4G,3H                                                                             3G  3G                                Cassia  5G  6G  7G  7G  6G  8G,4C                                                                             5G  9G,8C                                                                             7G  9G,8C                             Teaweed 3G  4G,3H                                                                             5G,3H                                                                             6G,4C                                                                             5G  8G,8C                                                                             4G  9G,9C                                                                             3G  4G                                Velvetleaf                                                                            6G,5H                                                                             8G,5H                                                                             7G,5H                                                                             8G,8C                                                                             5G,3H                                                                             6G,5H                                                                             5G,5H                                                                             7G,5H                                                                             3H  5G,3H                             Jimsonweed                                                                            3G  8G,3H                                                                             7G  8G,7C                                                                             8G  9G,8C                                                                             5G,3C                                                                             6G,5C                                                                             2G  8G,5C                             Soybean 2G  4G,2H                                                                             5G,3H                                                                             7G,5H                                                                             5G  7G,5H                                                                             4G,2H                                                                             7G,7C                                                                             4G,2H                                                                             6G,5C                             Rice    7G  10C 10E 10E 10E 10E 8G  10E 8G,3H                                                                             10E                               Wheat   2G  7G,3H                                                                             8G  9G,8C                                                                             6G  8G,8C                                                                             2G  3G  2G  3G                                __________________________________________________________________________

Test C

Twenty-five cm diameter plastic pots filled with Fallsington slit loamwere planted with soybeans, cotton, alfalfa, corn, rice, wheat, sorghum,velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata),sicklepod (Cassia obtusifolia), morningglory (Ipomoea hederacea),jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum),crabgrass (Digitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass(Echinochloa crusgalli), johnsongrass (Sorghum halepense), fieldbindweed (Convolvulus arvensis), giant foxtail (Setaria faberii) andwild oats (Avena fatua). Approximately 21/2 weeks after planting, theyoung plants and the soil around them were sprayed overall with the testchemicals dissolved in a non-pytotoxic solvent. Fourteen days aftertreatment, all species were compared to untreated controls and visuallyrated for response to treatment. The rating system was as describedpreviously for Test A. The data are presented in Table C. Again, severalof the compounds are characterized by a very high level ofpost-emergence activity.

                                      TABLE C                                     __________________________________________________________________________    Over-the-Top Soil/Foliage Treatment                                                   Compound 1  Compound 2                                                                             Compound 3                                                                             Compound 5  Compound 6                  Rate kg/ha                                                                            .063                                                                              .016                                                                              .004                                                                              .063 .016                                                                              .063 .016                                                                              .063                                                                              .016                                                                              .004                                                                              .063                                                                              .016                    __________________________________________________________________________    Soybeans                                                                              8G,2C                                                                             7G  0   10G,4C                                                                             9G,4C                                                                             10G,5C                                                                             9G,2C                                                                             9G,4C                                                                             8G,2C                                                                             6G  9G,2C                                                                             9G,2C                   Velvetleaf                                                                            9G  7G  3G  9G   9G,4C                                                                             9G,3C                                                                              6G  10C 4G  5G  7G  0                       Sesbania                                                                              9G,2C                                                                             8G  4G  10C  10C 10C  9G,3C                                                                             10C 9G,4C                                                                             7G  10C 8G                      Cassia  8G  7G  0   9G   3G  9G,3C                                                                              2G  9G  3G  4G  7G  0                       Cotton  9G,2C                                                                             9G  0   10C  8G,8C                                                                             10C  2G  10C 5G  2G  9G,2C                                                                             7G                      Morningglory                                                                          4G  6G  0   8G   8G  9G   0   8G  3G  0   6C  2G                      Alfalfa 5G  5G  0   9G,9C                                                                              8G,4C                                                                             9G,9C                                                                              3G  9G,9C                                                                             5G  0   8G,6C                                                                             0                       Jimsonweed                                                                            4G  5G  0   9G   7G  10C  7G  9G,1C                                                                             9G  2G  9G  4G                      Cocklebur                                                                             8G  8G  0   9G   0   9G   4G  6G  --  0   5G  1G                      Sunflower                                                                             10P 8G,3C                                                                             2G  9G,9C                                                                              7G,5C                                                                             8G   4G  8G,1H                                                                             6G,1H                                                                             1H  4G,1H                                                                             0                       Mustard 8G  8G,3C                                                                             0   9G,9C                                                                              10C 9G,9C                                                                              9G  10C 9G,3C                                                                             5G  10C 5G                      Sugarbeets                                                                            7G  7G  0   9G   9G  10C  8G  10C 8G  8G  10C 8G,2C                   Corn    8G,4U                                                                             6G,3H                                                                             3G,3H                                                                             9G,2C                                                                              9G,2C                                                                             8G,5C                                                                              8G  8G,3C                                                                             7G,3H                                                                             2G,2H                                                                             8G,8C                                                                             7G,2H                   Crabgrass                                                                             0   0   0   6G   2G  0    0   0   0   0   0   0                       Rice    7G,3C                                                                             4G,2C                                                                             2G  9G,8C                                                                              9G,7C                                                                             7G   3G  6G  2G  0   8G  3G                      Nutsedge                                                                              9G,4C                                                                             7G,2C                                                                             5G,1H                                                                             9G,9C                                                                              8G  7G   3G  3G  9G  5G  3G  0                       Barnyardgrass                                                                         9G,4C                                                                             7G,2C                                                                             3G,2H                                                                             9G,9C                                                                              9G,8C                                                                             9G,9C                                                                              9G,9C                                                                             7G  0   0   9G,6C                                                                             3G                      Wheat   7G  5G  3G  7G,6U                                                                              7G,6C                                                                             9G,9C                                                                              6G  7G  2G  0   8G,2C                                                                             4G                      Giant foxtail                                                                         7G  4G  2G  9G,7C                                                                              9G,2C                                                                             9G,4C                                                                              7G  6G  0   0   5G  4G                      Wild Oats                                                                             7G,2C                                                                             6G  3G,2C                                                                             8G   8G  7G   5G  0   3G  0   4G  0                       Sorghum 8G,2U                                                                             6G  6G  8G,4C                                                                              9G  8G,6C                                                                              8G  7G,2U                                                                             5G,1H                                                                             0   7G  5G                      Johnsongrass                                                                          6G,5U                                                                             7G,2U                                                                             7G,2C                                                                             8G,4U                                                                              8G,4U                                                                             8G,6U                                                                              8G,3U                                                                             6G  4G  0   7G,2U                                                                             3G                      Field Bindwind                                                                        3G  2G  0   8G   4G  4G   7G  4G  0   0   7G  0                       __________________________________________________________________________

Test D

Two ten-inch in diameter plastic pans lined with polyethylene linerswere filled with prepared Woodstown sandy loam. One pan was planted withseeds of wheat (Triticum aestivum), barley (Hordeum vulgare), wild oats(Avena fatua), downy brome (Bromus tectorum), cheatgrass (Bromussecalinus), blackgrass (Alopecurus myosuroides), annual bluegrass (Poaannua), green foxtail (Setaria viridis), quackgrass (Agropyron repens),Italian ryegrass (Lolium multiflorum) and ripgut brome (Bromus rigidus).The other pan was planted with seeds of Russian thistle (Salsola kali),tansy mustard (Descurania pinnata), Cleavers Galium aparine, tumblemustard (Sisymbrium altissium), kochia (Kochia scoparia), shepherd'spurse (Capsella bursapastoris), Matricaria inodora, black nightshade(Solanum nigrum), yellow rocket (Barbarea vulgaris), rapeseed (Brassicanapus) and wild buckwheat (Polygonum convolvulus). The above two panswere treated pre-emergence. At the same time two pans in which the aboveplant species were growing were treated post-emergence. Plant height atthe time of treatment ranged from 1-15 cm depending on plant species.

The compounds applied were diluted with a non-phytotoxic solvent andsprayed over-the-top of the pans. An untreated control and a solventalone control were included for comparison. All treatments weremaintained in the greenhouse for 19-21 days at which time the treatmentswere compared to the controls and the effects visually rated. Therecorded data are presented in Table D.

                  TABLE D                                                         ______________________________________                                                  Compound 1                                                                    Pre-Emergence                                                                             Post-Emergence                                          Rate kg/ha  0.015    0.06     0.015  0.06                                     ______________________________________                                        wheat       1G       5G       0      7G                                       barley      1G       5G       0      6G                                       wild oats   1G       7G       1C     8G                                       downy brome 5G       7G       8G     7G                                       cheatgrass  6G       9G       3C,8G  8C,9G                                    blackgrass  5G       8G       2C,7G  3C,8G                                    annual bluegrass                                                                          3G       7G       2C,7G  8C,9G                                    green foxtail                                                                             0        2G       2C,2G  2C,8G                                    quackgrass  2G       8G       7G     9C,9G                                    Italian ryegrass                                                                          3G       2C,8G    2C,8G  8C,8G                                    ripgut brome                                                                              6G       2C,8G    1C,7G  8C,9G                                    Russian thistle                                                                           0        2G       0      2C,2G                                    tansy mustard                                                                             9G       9C       5C,7G  9C,9G                                    Galium aparine                                                                            2C       2U,5G    3G     7G                                       tumble mustard                                                                            3C,8G    9C       8G     10C                                      kochia      7G       8G       6G     5C,8G                                    shepherd's purse                                                                          8G       9C       6G     8G                                       Matricaria inodora                                                                        7G       9G       0      0                                        Black nightshade                                                                          8G       8G       6G     7G                                       yellow rocket                                                                             7G       8G       4G     2U,7G                                    rapeseed    7G       9G       7G     10C                                      wild buckwheat                                                                            3G       4G       1C,3G  2C,7G                                    ______________________________________                                    

What is claimed is:
 1. A compound of the formula: ##STR73## where L is##STR74## R is F, Cl, Br, C₁ -C₃ alkyl, CO₂ R₄, C(O)SR₈, C(O)NR₅ R₆ orS(O)_(m) R₇ ;R₁ is H, F, Cl, Br or C₁ -C₃ alkyl; R₂ is H, F, Cl, Br orC₁ -C₃ alkyl; R₃ is H or CH₃ ; R₄ is C₁ -C₄ alkyl, CH₂ CH₂ OCH₃, CH₂ CH₂Cl or CH₂ CH═CH₂ ; R₅ is H or C₁ -C₃ alkyl; R₆ is C₁ -C₃ alkyl; or R₅and R₆ may be taken together to form --(CH₂)₄ --, --(CH₂)₅ -- or--(CH₂)₂ O(CH₂)₂ --; R₇ is C₁ -C₃ alkyl; R₈ is C₁ -C₄ alkyl; m is 0, 1or 2; X is CH₃ or OCH₃ ; Y is CH₃, C₂ H₅, CH₂ OCH₃, OCH₃, OC₂ H₅, NH₂,NHCH₃, N(CH₃)₂, CH(OCH₃)₂ or ##STR75## and their agriculturally suitablesalts; provided that: (1) when R is halogen and R₁ and/or R₂ arehalogen, then the values of R, R₁ and R₂ must be the same; (2) when R₁and R₂ are halogen, then the values of R₁ and R₂ must be the same; (3)the total number of carbon atoms of R₅ and R₆ is less than or equal to5; (4) R₁ and R₂ are not simultaneously H.
 2. Compounds of claim 1 whereL is ##STR76##
 3. Compounds of claim 2 where:R is Cl, Br, C₁ -C₃ alkyl,CO₂ R₄ or SO₂ R₇ ; R₄ is C₁ -C₃ alkyl; and R₃ is H.
 4. Compounds ofclaim 3 where R is CO₂ R₄.
 5. Compounds of claim 1 where L is ##STR77##6. Compounds of claim 5 whereR is CO₂ R₄ ; R₄ is C₁ -C₃ alkyl; and R₃ isH.
 7. Compounds of claim 1 where L is ##STR78##
 8. Compounds of claim 7whereR is CO₂ R₄ ; R₄ is C₁ -C₃ alkyl; and R₃ is H.
 9. The compound ofclaim 1,2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylicacid, methyl ester.
 10. The compound of claim 1,2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aaminosulfonyl]-1-cyclopentene-1-carboxylicacid, methyl ester.
 11. The compound of claim 1,2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-cyclopentene-1-carboxylicacid, methyl ester.
 12. A composition suitable for controlling thegrowth of undesired vegetation which comprises an effective amount of acompound of claim 1 and at least one of the following: surfactant, solidor liquid inert diluent.
 13. A composition suitable for controlling thegrowth of undesired vegetation which comprises an effective amount of acompound of claim 5 and at least one of the following: surfactant, solidor liquid inert diluent.
 14. A composition suitable for controlling thegrowth of undesired vegetation which comprises an effective amount of acompound of claim 7 and at least one of the following: surfactant, solidor liquid inert diluent.
 15. A composition suitable for controlling thegrowth of undesired vegetation which comprises an effective amount of acompound of claim 8 and at least one of the following: surfactant, solidor liquid inert diluent.
 16. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 1. 17. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim5.
 18. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 8. 19. A compound of the formula: ##STR79## where L is##STR80## R is F, Cl, Br, C₁ -C₃ alkyl, CO₂ R₄, C(O)SR₈, C(O)NR₅ R₆ orS(O)_(m) R₇ ;R₃ is H or CH₃ ; R₄ is C₁ -C₄ alkyl, CH₂ CH₂ OCH₃, CH₂ CH₂Cl or CH₂ CH═CH₂ ; R₅ is H or C₁ -C₃ alkyl; R₆ is C₁ -C₃ alkyl; or R₅and R₆ may be taken together to form --(CH₂)₄ --, --(CH₂)₅ -- or--(CH₂)₂ O(CH₂)₂ --; R₇ is C₁ -C₃ alkyl; R₈ is C₁ -C₄ alkyl; m is 0, 1or 2; X is CH₃ or OCH₃ ; Y is CH₃, C₂ H₅, CH₂ OCH₃, OCH₃, OC₂ H₅, NH₂,NHCH₃, N(CH₃)₂, CH(OCH₃)₂ or ##STR81## and their agriculturally suitablesalts; provided that the total number of carbon atoms of R₅ and R₆ isless than or equal to 5.